Carbonyl Ylide Cycloaddition Approach to Platensimycin

Carbonyl Ylide Cycloaddition Approach to Platensimycin

Short and to the point: A formal synthesis of platensimycin has been accomplished by employing a carbonyl ylide [3+2] cycloaddition reaction (see scheme). This short and facile enantioselective synthesis of the pivotal tetracyclic precursor requires 11 steps and proceeds in 20 % overall yield from i...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2008-05, Vol.47 (21), p.4009-4011
Hauptverfasser: Kim, Chan Hyuk, Jang, Ki Po, Choi, Soo Young, Chung, Young Keun, Lee, Eun
Format: Artikel
Sprache:eng
Schlagworte:
Acetates - chemistry
Acetonitriles - chemistry
Adamantane - chemical synthesis
Adamantane - chemistry
Alkenes - chemistry
Aminobenzoates - chemical synthesis
Aminobenzoates - chemistry
Anilides - chemical synthesis
Anilides - chemistry
antibiotics
carbonyl ylides
Catalysis
Cyclization
Molecular Structure
natural products
Rhodium - chemistry
Stereoisomerism
total synthesis
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Zusammenfassung:Short and to the point: A formal synthesis of platensimycin has been accomplished by employing a carbonyl ylide [3+2] cycloaddition reaction (see scheme). This short and facile enantioselective synthesis of the pivotal tetracyclic precursor requires 11 steps and proceeds in 20 % overall yield from isopropyl cyanoacetate.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200800568